When Jay Rockman’s mother spotted Ashley Reich on the schoolyard and asked her seventh-grade son who the cute new girl was, he never could have imagined they’d one day be exchanging vows. “We ended up becoming good friends but didn’t start dating until 11th grade,” explains Jay. After 10 years together, he was ready to take the next step in their relationship and asked her parents for their blessing. “Ashley and I were totally enmeshed in each other’s families – we were already family to one another,” he smiles. “There’s never been a doubt in my mind that she’s the person I would end up with.”

As the executive relationships editor of The Huffington Post, it was no wonder Ashley’s job played a part in her proposal. She thought it was a typical morning at home as she read through pitches from her team, but it wasn’t. “The last pitch was a link to a YouTube video titled ‘High School Sweetheart Proposes to Longtime Girlfriend.’ I clicked the link and saw a video of myself, sitting in the very spot I was currently in,” declares Ashley, who turned to Jay confused. “He said something I have no recollection of, got down on one knee, and presented the most beautiful ring I’ve ever seen.” The rest of the day was filled with more surprises, including lunch at the restaurant where they had their first date and celebrations with loved ones.

When it came to wedding planning, Ashley enlisted the help of one of her best friends, Paige Blatt, who works with Debbie Geller of Geller Events. “She totally understood my taste, knew our families and what they wanted, and all our meetings were just like we were hanging out. I loved it!” exclaims the bride. Since Ashley has viewed countless photos of nuptials through work, there were a couple of nonnegotiable items on her wish list – one of which being an alfresco ceremony and reception. Though they originally wrote off their venue since it was across the street from their high school and therefore “too close to home,” the setting ended up being one of their favorite parts of the day and even gave them the opportunity to have their “first look” at the very place they first saw each other.

On the evening of the ceremony, an aisle runner lined with hydrangeas, spiral eucalyptus, and candlelight led to a chuppah positioned in front of a dramatic floral wall covered with greenery, ivory wisteria, and Southern smilax. “Jay’s mom encouraged us to dream big when it came to florals and ceremony décor, and both turned out amazing thanks to The Hidden Garden,” reveals Ashley. To the romantic sounds of a string trio, Jay walked down the aisle with his parents. Three flower girls followed, with one carrying a very special token: “One of our flower girls is the daughter of the flower girl from my parents’ wedding, and she carried the very same basket!” notes Ashley. Regardless of gender, bridesmaids and groomsmen stood on either side of the chuppah to commemorate their friendships with both Ashley and Jay. At last, the bride emerged in a beautiful gown featuring an illusion neckline and held a bouquet of snowy peonies to “Kissing You” from the Romeo + Juliet soundtrack, which held special significance to the duo since they first watched the film together in eighth grade.

During the service, which was led by a rabbi who the bride has known since birth, the couple was wrapped in a tallit made by Jay’s grandfather and used the kiddush cup Ashley gifted Jay at his bar mitzvah when they were just 13 years old. “The ceremony was the most meaningful, emotional, and beautiful moment of my life,” recalls the groom. “We had waited so long to get there and it felt so natural to be there with Ashley surrounded by our family and friends.” Muses the bride, “I love that we wrote personalized vows… I got so choked up at the start, I was worried I wouldn’t be able to even get them out!”

The design of the open-air reception was inspired by the floral envelope liner on the invitation suite, which was also used for the menus and escort cards featuring mini envelopes with table assignments inside. The flower motif was additionally incorporated on the dance floor by way of a beautifully detailed decal. Blush linens covered tables, which were surrounded by Lucite chairs and decorated with high and low centerpieces. Arrangements were brimming with textured greens including gardenia leaves and cascading amaranthus, as well as roses, lisianthus blossoms, hydrangeas, helleborus blooms, and Café au Lait dahlias.

Framed photos taken of the couple from grade school and beyond were placed on the escort card table along with snapshots of what they had written in each other’s yearbooks over the years – a total surprise to the bride. Paper goods, including table numbers and cocktail napkins, were also representative of milestones throughout their relationship. To keep their families at the heart of the day, their first dance to “Lucky” by Jason Mraz was followed by both a father-daughter dance and a mother-son dance. “My mom is one of the most important people in the world to me and dancing with her on that day meant a lot,” shares Jay.

The rest of the reception was filled with dinner and dancing to Motown, oldies, and modern-day hits from a live band and a DJ. In addition to the wedding confection, guests were sent home with miniature cakes made by the bride’s grandmother, who baked smaller versions of her famous treat, which is a hit at every special event. A note attached read, “Made with love by Grandma” to make the day even more rooted in family.